Protopine (BioDeep_00000397983)

Main id: BioDeep_00000000076

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


Protopine

化学式: C20H19NO5 (353.1263)
中文名称: 原阿片碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3
InChI: InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3

描述信息

Annotation level-1
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.601
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors
D002491 - Central Nervous System Agents > D000700 - Analgesics
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.596
IPB_RECORD: 1441; CONFIDENCE confident structure
Protopine (Corydinine), an isoquinoline alkaloid, is a specific reversible and competitive inhibitor of acetylcholinesterase. Protopine exhibits anti-inflammation, anti-microbial, anti-angiogenic and anti-tumour activity[1][2].
Protopine (Corydinine), an isoquinoline alkaloid, is a specific reversible and competitive inhibitor of acetylcholinesterase. Protopine exhibits anti-inflammation, anti-microbial, anti-angiogenic and anti-tumour activity[1][2].

同义名列表

4 个代谢物同义名

Protopine; Corydinine; Protopine; Protopine



数据库引用编号

41 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

544 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 8 BCL2, CASP3, MAPK14, MARK2, PIK3CA, PTGS2, SMAD1, TUBB4B
Peripheral membrane protein 3 ACHE, CYP1B1, PTGS2
Endoplasmic reticulum membrane 3 BCL2, CYP1B1, PTGS2
Nucleus 7 ACHE, BCL2, CASP3, MAPK14, SMAD1, TGFBR1, TUBB4B
cytosol 7 BCL2, CASP3, LEP, MAPK14, PIK3CA, SMAD1, TUBB4B
dendrite 3 BMPR1B, BMPR2, MARK2
nucleoplasm 5 BMPR2, CASP3, MAPK14, MARK2, SMAD1
Cell membrane 5 ACHE, BMPR1B, BMPR2, TGFBR1, TNF
lamellipodium 1 PIK3CA
Synapse 1 ACHE
cell surface 4 ACHE, BMPR2, TGFBR1, TNF
glutamatergic synapse 2 CASP3, MAPK14
Golgi apparatus 1 ACHE
neuromuscular junction 1 ACHE
neuronal cell body 4 BMPR1B, BMPR2, CASP3, TNF
endosome 1 TGFBR1
plasma membrane 9 ACHE, ACVR1, BCHE, BMPR1B, BMPR2, MARK2, PIK3CA, TGFBR1, TNF
Membrane 8 ACHE, ACVR1, BCL2, BMPR1B, CYP1B1, MARK2, SMAD1, TGFBR1
apical plasma membrane 1 BMPR2
axon 1 BMPR2
caveola 2 BMPR2, PTGS2
extracellular exosome 1 TUBB4B
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 8 ACHE, BCHE, BMP4, BMP7, BMPR2, INHBE, LEP, TNF
perinuclear region of cytoplasm 2 ACHE, PIK3CA
Cell junction, tight junction 1 TGFBR1
adherens junction 1 BMPR2
bicellular tight junction 1 TGFBR1
intercalated disc 1 PIK3CA
mitochondrion 4 BCL2, CYP1B1, MAPK14, MARK2
protein-containing complex 3 BCL2, PTGS2, SMAD1
intracellular membrane-bounded organelle 1 CYP1B1
Microsome membrane 2 CYP1B1, PTGS2
postsynaptic density 2 BMPR2, CASP3
Single-pass type I membrane protein 3 ACVR1, BMPR1B, TGFBR1
Secreted 6 ACHE, BCHE, BMP4, BMP7, INHBE, LEP
extracellular region 8 ACHE, BCHE, BMP4, BMP7, LEP, MAPK14, TNF, TUBB4B
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Extracellular side 1 ACHE
transcription regulator complex 1 SMAD1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
Extracellular vesicle 1 TUBB4B
microtubule cytoskeleton 1 TUBB4B
apical part of cell 1 ACVR1
clathrin-coated pit 1 BMPR2
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 BMP7
Membrane raft 2 TGFBR1, TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 TUBB4B
microtubule 1 TUBB4B
basement membrane 1 ACHE
collagen-containing extracellular matrix 2 BMP7, INHBE
lateral plasma membrane 1 MARK2
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 2 PTGS2, SMAD1
nuclear outer membrane 1 PTGS2
receptor complex 3 BMPR1B, BMPR2, TGFBR1
neuron projection 1 PTGS2
chromatin 1 SMAD1
phagocytic cup 1 TNF
mitotic spindle 1 TUBB4B
cytoskeleton 1 TUBB4B
spindle pole 1 MAPK14
actin filament 1 MARK2
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 ACHE
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
axonemal microtubule 1 TUBB4B
Cell projection, dendrite 1 MARK2
side of membrane 1 ACHE
myelin sheath 1 BCL2
basal plasma membrane 1 BMPR2
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
HFE-transferrin receptor complex 1 BMPR1B
endoplasmic reticulum lumen 3 BCHE, BMP4, PTGS2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
azurophil granule lumen 1 TUBB4B
nuclear envelope lumen 1 BCHE
heteromeric SMAD protein complex 1 SMAD1
SMAD protein complex 1 SMAD1
synaptic cleft 1 ACHE
death-inducing signaling complex 1 CASP3
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
BAD-BCL-2 complex 1 BCL2
BMP receptor complex 1 ACVR1
[Isoform H]: Cell membrane 1 ACHE
activin receptor complex 2 ACVR1, TGFBR1
transforming growth factor beta ligand-receptor complex 1 TGFBR1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
microtubule bundle 1 MARK2
homomeric SMAD protein complex 1 SMAD1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Hongjie Chen, Yiming Zhong, Weilin Sang, Cong Wang, Haiming Lu, Peng Lai, Libo Zhu, Jinzhong Ma. Protopine protects chondrocytes from undergoing ferroptosis by activating Nrf2 pathway. Biochemical and biophysical research communications. 2024 May; 710(?):149599. doi: 10.1016/j.bbrc.2024.149599. [PMID: 38608493]
  • Meishan Yue, Jialu Huang, Xiaolan Ma, Peng Huang, Yisong Liu, Jianguo Zeng. Protopine Alleviates Dextran Sodium Sulfate-Induced Ulcerative Colitis by Improving Intestinal Barrier Function and Regulating Intestinal Microbiota. Molecules (Basel, Switzerland). 2023 Jul; 28(13):. doi: 10.3390/molecules28135277. [PMID: 37446938]
  • Sravan Gopalkrishnashetty Sreenivasmurthy, Ashok Iyaswamy, Senthilkumar Krishnamoorthi, Sanjib Senapati, Sandeep Malampati, Zhou Zhu, Cheng-Fu Su, Jia Liu, Xin-Jie Guan, Benjamin Chun-Kit Tong, King-Ho Cheung, Jie-Qiong Tan, Jia-Hong Lu, Siva Sundara Kumar Durairajan, Ju-Xian Song, Min Li. Protopine promotes the proteasomal degradation of pathological tau in Alzheimer's disease models via HDAC6 inhibition. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Feb; 96(?):153887. doi: 10.1016/j.phymed.2021.153887. [PMID: 34936968]
  • Xiaohui Zhang, Yule Wang, Kai Zhang, Hongda Sheng, Yuhan Wu, Huimin Wu, Yingchao Wang, Jianli Guan, Qingfen Meng, Huahuan Li, Zhenhao Li, Guanwei Fan, Yi Wang. Discovery of tetrahydropalmatine and protopine regulate the expression of dopamine receptor D2 to alleviate migraine from Yuanhu Zhitong formula. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Oct; 91(?):153702. doi: 10.1016/j.phymed.2021.153702. [PMID: 34419734]
  • Tian-Hua Wu, Jun-Hui Zhou, Yu-Yang Zhao, Yu-Jie Wei, Fang Chen, Yong-Fu Gong, Yuan Yuan, Lu-Qi Huang. [Genetic diversity of protopine-6-hydroxylase in three medicinal Papaver plants]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2021 Aug; 46(16):4111-4116. doi: 10.19540/j.cnki.cjcmm.20210522.102. [PMID: 34467721]
  • K B Pandeya, Aditya Ganeshpurkar, Mahendra Kumar Mishra. Natural RNA dependent RNA polymerase inhibitors: Molecular docking studies of some biologically active alkaloids of Argemone mexicana. Medical hypotheses. 2020 Nov; 144(?):109905. doi: 10.1016/j.mehy.2020.109905. [PMID: 32535456]
  • Beibei Zhang, Mengnan Zeng, Meng Li, Yuxuan Kan, Benke Li, Ruiqi Xu, Yuanyuan Wu, Shengchao Wang, Xiaoke Zheng, Weisheng Feng. Protopine Protects Mice against LPS-Induced Acute Kidney Injury by Inhibiting Apoptosis and Inflammation via the TLR4 Signaling Pathway. Molecules (Basel, Switzerland). 2019 Dec; 25(1):. doi: 10.3390/molecules25010015. [PMID: 31861525]
  • Jerald J Nair, Johannes van Staden. Antiprotozoal alkaloid principles of the plant family Amaryllidaceae. Bioorganic & medicinal chemistry letters. 2019 10; 29(20):126642. doi: 10.1016/j.bmcl.2019.126642. [PMID: 31515186]
  • Minghui Sun, Lingling Zhao, Kai Wang, Lida Han, Jihao Shan, Liming Wu, Xiaofeng Xue. Rapid identification of 'mad honey' from Tripterygium wilfordii Hook. f. and Macleaya cordata (Willd) R. Br using UHPLC/Q-TOF-MS. Food chemistry. 2019 Oct; 294(?):67-72. doi: 10.1016/j.foodchem.2019.05.028. [PMID: 31126506]
  • Cuiting Wu, Xin Wang, Ming Xu, Youping Liu, Xin Di. Intracellular Accumulation as an Indicator of Cytotoxicity to Screen Hepatotoxic Components of Chelidonium majus L. by LC-MS/MS. Molecules (Basel, Switzerland). 2019 Jun; 24(13):. doi: 10.3390/molecules24132410. [PMID: 31261913]
  • Younglim Son, Younju An, Jaeyeon Jung, Sora Shin, InWha Park, Jungsug Gwak, Bong Gun Ju, Young-Hwa Chung, MinKyun Na, Sangtaek Oh. Protopine isolated from Nandina domestica induces apoptosis and autophagy in colon cancer cells by stabilizing p53. Phytotherapy research : PTR. 2019 Jun; 33(6):1689-1696. doi: 10.1002/ptr.6357. [PMID: 30932278]
  • Ke Li, Junfang Li, Jin Su, Xuefeng Xiao, Xiujuan Peng, Feng Liu, Defeng Li, Yi Zhang, Tao Chong, Haiyu Xu, Changxiao Liu, Hongjun Yang. Identification of quality markers of Yuanhu Zhitong tablets based on integrative pharmacology and data mining. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 May; 44(?):212-219. doi: 10.1016/j.phymed.2018.03.002. [PMID: 29551644]
  • Hongbing Zhang, Xin Wu, Jun Xu, Suxiao Gong, Yanqi Han, Tiejun Zhang, Changxiao Liu. The comparative pharmacokinetic study of Yuanhu Zhitong prescription based on five quality-markers. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 May; 44(?):148-154. doi: 10.1016/j.phymed.2018.02.005. [PMID: 29523382]
  • Ya-Jun Huang, Pi Cheng, Zhuo-Yi Zhang, Shi-Jie Tian, Zhi-Liang Sun, Jian-Guo Zeng, Zhao-Ying Liu. Biotransformation and tissue distribution of protopine and allocryptopine and effects of Plume Poppy Total Alkaloid on liver drug-metabolizing enzymes. Scientific reports. 2018 01; 8(1):537. doi: 10.1038/s41598-017-18816-7. [PMID: 29323165]
  • Elsayed Mickdam, Ratchaneewan Khiaosa-Ard, Barbara U Metzler-Zebeli, Fenja Klevenhusen, Remigius Chizzola, Qendrim Zebeli. Rumen microbial abundance and fermentation profile during severe subacute ruminal acidosis and its modulation by plant derived alkaloids in vitro. Anaerobe. 2016 Jun; 39(?):4-13. doi: 10.1016/j.anaerobe.2016.02.002. [PMID: 26868619]
  • Vamshi K Manda, Mohamed A Ibrahim, Olivia R Dale, Mallika Kumarihamy, Stephen J Cutler, Ikhlas A Khan, Larry A Walker, Ilias Muhammad, Shabana I Khan. Modulation of CYPs, P-gp, and PXR by Eschscholzia californica (California Poppy) and Its Alkaloids. Planta medica. 2016 Apr; 82(6):551-8. doi: 10.1055/s-0042-103689. [PMID: 27054913]
  • Rica Capistrano I, An Wouters, Filip Lardon, Claudia Gravekamp, Sandra Apers, Luc Pieters. In vitro and in vivo investigations on the antitumour activity of Chelidonium majus. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2015 Dec; 22(14):1279-87. doi: 10.1016/j.phymed.2015.10.013. [PMID: 26626193]
  • Lidiya Georgieva, Ivan Ivanov, Andrey Marchev, Ina Aneva, Panteley Denev, Vasil Georgiev, Atanas Pavlov. Protopine production by fumaria cell suspension cultures: effect of light. Applied biochemistry and biotechnology. 2015 May; 176(1):287-300. doi: 10.1007/s12010-015-1574-6. [PMID: 25820387]
  • Tsvetelina Doncheva, Amgalan Solongo, Nadezhda Kostova, Yadamsuren Gerelt-Od, Dangaa Selenge, Stefan Philipov. Leptopyrine, new alkaloid from Leptopyrum fumarioides L. (Ranunculaceae). Natural product research. 2015; 29(9):853-6. doi: 10.1080/14786419.2014.991322. [PMID: 25529023]
  • Jia-jia Yu, Deng-li Cong, Ying Jiang, Yuan Zhou, Yan Wang, Chun-fang Zhao. [Study on alkaloids of Corydalis ochotensis and their antitumor bioactivity]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Oct; 37(10):1795-8. doi: . [PMID: 25895386]
  • C Moser, S P Vickers, R Brammer, S C Cheetham, J Drewe. Antidiabetic effects of the Cimicifuga racemosa extract Ze 450 in vitro and in vivo in ob/ob mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Sep; 21(11):1382-9. doi: 10.1016/j.phymed.2014.06.002. [PMID: 25022210]
  • Xiaochen Huang, Shulan Su, Wenxia Cui, Pei Liu, Jin-Ao Duan, Jianming Guo, Zhenhao Li, Erxin Shang, Dawei Qian, Zhijun Huang. Simultaneous determination of paeoniflorin, albiflorin, ferulic acid, tetrahydropalmatine, protopine, typhaneoside, senkyunolide I in Beagle dogs plasma by UPLC-MS/MS and its application to a pharmacokinetic study after Oral Administration of Shaofu Zhuyu Decoction. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jul; 962(?):75-81. doi: 10.1016/j.jchromb.2014.05.032. [PMID: 24907546]
  • Kai He, Jian-Li Gao. Protopine inhibits heterotypic cell adhesion in MDA-MB-231 cells through down-regulation of multi-adhesive factors. African journal of traditional, complementary, and alternative medicines : AJTCAM. 2014; 11(2):415-24. doi: 10.4314/ajtcam.v11i2.28. [PMID: 25435628]
  • Phurpa Wangchuk, Wangchuk Phurpa, Paul A Keller, Stephen G Pyne, Wilford Lie, Anthony C Willis, Roonglawan Rattanajak, Sumalee Kamchonwongpaisan. A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain. Journal of ethnopharmacology. 2013 Dec; 150(3):953-9. doi: 10.1016/j.jep.2013.09.052. [PMID: 24120516]
  • Lamine Bournine, Sihem Bensalem, Jean-Noël Wauters, Mokrane Iguer-Ouada, Fadila Maiza-Benabdesselam, Fatiha Bedjou, Vincent Castronovo, Akeila Bellahcène, Monique Tits, Michel Frédérich. Identification and quantification of the main active anticancer alkaloids from the root of Glaucium flavum. International journal of molecular sciences. 2013 Dec; 14(12):23533-44. doi: 10.3390/ijms141223533. [PMID: 24317429]
  • Sanggil Choe, Eunjung Lee, Gang-nam Jin, Yang Han Lee, Soo Young Kim, Hwakyung Choi, Heesun Chung, Bang Yeon Hwang, Suncheun Kim. Genetic and chemical components analysis of Papaver setigerum naturalized in Korea. Forensic science international. 2012 Oct; 222(1-3):387-93. doi: 10.1016/j.forsciint.2012.08.002. [PMID: 22921420]
  • Hongda Ma, Qingchun Zhao, Yongjun Wang, Tao Guo, Ye An, Guobing Shi. Design and evaluation of self-emulsifying drug delivery systems of Rhizoma corydalis decumbentis extracts. Drug development and industrial pharmacy. 2012 Oct; 38(10):1200-6. doi: 10.3109/03639045.2011.643897. [PMID: 22512784]
  • Phurpa Wangchuk, Paul A Keller, Stephen G Pyne, Anthony C Willis, Sumalee Kamchonwongpaisan. Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia. Journal of ethnopharmacology. 2012 Aug; 143(1):310-3. doi: 10.1016/j.jep.2012.06.037. [PMID: 22796506]
  • Xiaomeng Chen, Yingchun Zhang, Shuo Lin, Hongjun Yang, Hongwei Wu, Shaojing Li, Defeng Li, Haiyu Xu. [Study on absorption ingredients of yuanhuzhitong pill by everted intestinal sac method]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Jul; 37(13):2005-11. doi: . [PMID: 23019888]
  • Phurpa Wangchuk, Paul A Keller, Stephen G Pyne, Thanapat Sastraruji, Malai Taweechotipatr, Roonglawan Rattanajak, Aunchalee Tonsomboon, Sumalee Kamchonwongpaisan. Phytochemical and biological activity studies of the Bhutanese medicinal plant Corydalis crispa. Natural product communications. 2012 May; 7(5):575-80. doi: . [PMID: 22799079]
  • Najeeb-ur-Rehman, Malik Hassan Mehmood, Adnan J Al-Rehaily, Ramzi A A Mothana, Anwar H Gilani. Species and tissue-specificity of prokinetic, laxative and spasmodic effects of Fumaria parviflora. BMC complementary and alternative medicine. 2012 Mar; 12(?):16. doi: 10.1186/1472-6882-12-16. [PMID: 22405321]
  • Jiri Vrba, Eva Orolinova, Jitka Ulrichova. Induction of heme oxygenase-1 by Macleaya cordata extract and its constituent sanguinarine in RAW264.7 cells. Fitoterapia. 2012 Mar; 83(2):329-35. doi: 10.1016/j.fitote.2011.11.022. [PMID: 22166397]
  • Zhiying Dou, Kefeng Li, Ping Wang, Liu Cao. Effect of wine and vinegar processing of Rhizoma Corydalis on the tissue distribution of tetrahydropalmatine, protopine and dehydrocorydaline in rats. Molecules (Basel, Switzerland). 2012 Jan; 17(1):951-70. doi: 10.3390/molecules17010951. [PMID: 22258341]
  • Hefen Sun, Helei Hou, Ping Lu, Lixing Zhang, Fangyu Zhao, Chao Ge, Tingpu Wang, Ming Yao, Jinjun Li. Isocorydine inhibits cell proliferation in hepatocellular carcinoma cell lines by inducing G2/m cell cycle arrest and apoptosis. PloS one. 2012; 7(5):e36808. doi: 10.1371/journal.pone.0036808. [PMID: 22623962]
  • Ziming Lu, Wuxing Sun, Xuhong Duan, Zhiyun Yang, Yadong Liu, Pengfei Tu. [Chemical constituents from Corydalis yanhusuo]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Jan; 37(2):235-7. doi: . [PMID: 22737858]
  • Sarita Singh, Vidya Bhushan Pandey, Tryambak Deo Singh. Alkaloids and flavonoids of Argemone mexicana. Natural product research. 2012; 26(1):16-21. doi: 10.1080/14786419.2010.529809. [PMID: 21722040]
  • Xiao Wang, Hongjing Dong, Bin Yang, Dahui Liu, Wenjuan Duan, Luqi Huang. Preparative isolation of alkaloids from Dactylicapnos scandens using pH-zone-refining counter-current chromatography by changing the length of the separation column. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Dec; 879(31):3767-70. doi: 10.1016/j.jchromb.2011.10.013. [PMID: 22056347]
  • Ji Eun Park, To Dao Cuong, Tran Manh Hung, IkSoo Lee, MinKyun Na, Jin Cheol Kim, SungWoo Ryoo, Jeong Hyung Lee, Jae Sue Choi, Mi Hee Woo, Byung Sun Min. Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells. Bioorganic & medicinal chemistry letters. 2011 Dec; 21(23):6960-3. doi: 10.1016/j.bmcl.2011.09.128. [PMID: 22024033]
  • Yingchun Zhang, Haiyu Xu, Xiaomeng Chen, Chang Chen, Haijun Wang, Fanyun Meng, Hongjun Yang, Luqi Huang. Simultaneous quantification of 17 constituents from Yuanhu Zhitong tablet using rapid resolution liquid chromatography coupled with a triple quadrupole electrospray tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2011 Nov; 56(3):497-504. doi: 10.1016/j.jpba.2011.06.008. [PMID: 21733652]
  • Dong-Ung Lee, Jong Hee Park, Ludger Wessjohann, Jürgen Schmidt. Alkaloids from Papaver coreanum. Natural product communications. 2011 Nov; 6(11):1593-4. doi: . [PMID: 22224268]
  • Maria Kulp, Olga Bragina, Priit Kogerman, Mihkel Kaljurand. Capillary electrophoresis with LED-induced native fluorescence detection for determination of isoquinoline alkaloids and their cytotoxicity in extracts of Chelidonium majus L. Journal of chromatography. A. 2011 Aug; 1218(31):5298-304. doi: 10.1016/j.chroma.2011.06.016. [PMID: 21726876]
  • Orlando Muñoz, Philippe Christen, Sylvian Cretton, Nadine Backhouse, Vanessa Torres, Olosmira Correa, Edda Costa, Hugo Miranda, Carla Delporte. Chemical study and anti-inflammatory, analgesic and antioxidant activities of the leaves of Aristotelia chilensis (Mol.) Stuntz, Elaeocarpaceae. The Journal of pharmacy and pharmacology. 2011 Jun; 63(6):849-59. doi: 10.1111/j.2042-7158.2011.01280.x. [PMID: 21585384]
  • Lili Niu, Zhensheng Xie, Tanxi Cai, Peng Wu, Peng Xue, Xiulan Chen, Zhiyong Wu, Yoichiro Ito, Famei Li, Fuquan Yang. Preparative isolation of alkaloids from Corydalis bungeana Turcz. by high-speed counter-current chromatography using stepwise elution. Journal of separation science. 2011 May; 34(9):987-94. doi: 10.1002/jssc.201000785. [PMID: 21387560]
  • Kristýna Pěnčíková, Jana Urbanová, Pavel Musil, Eva Táborská, Jana Gregorová. Seasonal variation of bioactive alkaloid contents in Macleaya microcarpa (Maxim.) Fedde. Molecules (Basel, Switzerland). 2011 Apr; 16(4):3391-401. doi: 10.3390/molecules16043391. [PMID: 21512447]
  • Pavel Kosina, Jana Gregorova, Jiri Gruz, Jan Vacek, Milan Kolar, Mathias Vogel, Werner Roos, Kathrin Naumann, Vilim Simanek, Jitka Ulrichova. Phytochemical and antimicrobial characterization of Macleaya cordata herb. Fitoterapia. 2010 Dec; 81(8):1006-12. doi: 10.1016/j.fitote.2010.06.020. [PMID: 20600683]
  • Isabel Desgagné-Penix, Morgan F Khan, David C Schriemer, Dustin Cram, Jacek Nowak, Peter J Facchini. Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. BMC plant biology. 2010 Nov; 10(?):252. doi: 10.1186/1471-2229-10-252. [PMID: 21083930]
  • Lucie Cahlíková, Lubomír Opletal, Milan Kurfürst, Katerina Macáková, Andrea Kulhánková, Anna Hostálková. Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae). Natural product communications. 2010 Nov; 5(11):1751-4. doi: . [PMID: 21213973]
  • Gao-Xue Wang, Zhuang Zhou, Dong-Xin Jiang, Jing Han, Jian-Fu Wang, Liang-Wei Zhao, Jun Li. In vivo anthelmintic activity of five alkaloids from Macleaya microcarpa (Maxim) Fedde against Dactylogyrus intermedius in Carassius auratus. Veterinary parasitology. 2010 Aug; 171(3-4):305-13. doi: 10.1016/j.vetpar.2010.03.032. [PMID: 20413222]
  • Li Ouyang, Xiaoli Su, Dingsheng He, Yuanyuan Chen, Ming Ma, Qingji Xie, Shouzhuo Yao. A study on separation and extraction of four main alkaloids in Macleaya cordata (Willd) R. Br. with strip dispersion hybrid liquid membrane. Journal of separation science. 2010 Jul; 33(13):2026-34. doi: 10.1002/jssc.201000103. [PMID: 20512809]
  • Ming Zhong, Ke-Long Huang, Jian-Guo Zeng, Shuang Li, Jin-Ming She, Guiyin Li, Li Zhang. Optimization of microwave-assisted extraction of protopine and allocryptopine from stems of Macleaya cordata (Willd) R. Br. using response surface methodology. Journal of separation science. 2010 Jul; 33(14):2160-7. doi: 10.1002/jssc.201000085. [PMID: 20533346]
  • Xiaoying Liu, Qian Liu, Dongmei Wang, Xueya Wang, Peng Zhang, Haiyan Xu, Hui Zhao, Huaiqing Zhao. Validated liquid chromatography-tandem mass spectrometry method for quantitative determination of dauricine in human plasma and its application to pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 May; 878(15-16):1199-203. doi: 10.1016/j.jchromb.2010.03.028. [PMID: 20371215]
  • Phurpa Wangchuk, John B Bremner, Roonglawan Rattanajak, Sumalee Kamchonwongpaisan. Antiplasmodial agents from the Bhutanese medicinal plant Corydalis calliantha. Phytotherapy research : PTR. 2010 Apr; 24(4):481-5. doi: 10.1002/ptr.2893. [PMID: 19496064]
  • Deepak Singla, Arun Sharma, Jasjit Kaur, Bharat Panwar, Gajendra P S Raghava. BIAdb: a curated database of benzylisoquinoline alkaloids. BMC pharmacology. 2010 Mar; 10(?):4. doi: 10.1186/1471-2210-10-4. [PMID: 20205728]
  • Chen Wang, Shuowen Wang, Guorong Fan, Hanfa Zou. Screening of antinociceptive components in Corydalis yanhusuo W.T. Wang by comprehensive two-dimensional liquid chromatography/tandem mass spectrometry. Analytical and bioanalytical chemistry. 2010 Mar; 396(5):1731-40. doi: 10.1007/s00216-009-3409-1. [PMID: 20101504]
  • Wan-Suk Oh, Pan-Young Jeong, Hyoe-Jin Joo, Jeong-Eui Lee, Yil-Seong Moon, Hyang-Mi Cheon, Jung-Ho Kim, Yong-Uk Lee, Yhong-Hee Shim, Young-Ki Paik. Identification and characterization of a dual-acting antinematodal agent against the pinewood nematode, Bursaphelenchus xylophilus. PloS one. 2009 Nov; 4(11):e7593. doi: 10.1371/journal.pone.0007593. [PMID: 19907651]
  • Hao Liu, Jihua Wang, Jianglin Zhao, Shiqiong Lu, Jingguo Wang, Weibo Jiang, Zhanhong Ma, Ligang Zhou. Isoquinoline alkaloids from Macleaya cordata active against plant microbial pathogens. Natural product communications. 2009 Nov; 4(11):1557-60. doi: ". [PMID: 19967990]
  • Fuhua Wang, Xiao Hu, Hailin Chen, Jianping Ma, Jianxin Wang, Aijun Hou. [Alkaloids from Dactylicapnos scandens Hutch]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Aug; 34(16):2057-9. doi: . [PMID: 19938545]
  • Ying-Zhuang Chen, Guo-Zhu Liu, Yao Shen, Bo Chen, Jian-Guo Zeng. Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry. Journal of chromatography. A. 2009 Mar; 1216(11):2104-10. doi: 10.1016/j.chroma.2008.08.066. [PMID: 18774138]
  • Hongda Ma, Yongjun Wang, Tao Guo, Zhonggui He, Xinyu Chang, Xiaohui Pu. Simultaneous determination of tetrahydropalmatine, protopine, and palmatine in rat plasma by LC-ESI-MS and its application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2009 Feb; 49(2):440-6. doi: 10.1016/j.jpba.2008.11.019. [PMID: 19121909]
  • Xianghua Xiao, Juntian Liu, Jingwen Hu, Xiuping Zhu, Hua Yang, Chaoyun Wang, Yuanhui Zhang. Protective effects of protopine on hydrogen peroxide-induced oxidative injury of PC12 cells via Ca(2+) antagonism and antioxidant mechanisms. European journal of pharmacology. 2008 Sep; 591(1-3):21-7. doi: 10.1016/j.ejphar.2008.06.045. [PMID: 18602385]
  • Strahil Berkov, Jaume Bastida, Milena Nikolova, Francesc Viladomat, Carles Codina. Rapid TLC/GC-MS identification of acetylcholinesterase inhibitors in alkaloid extracts. Phytochemical analysis : PCA. 2008 Sep; 19(5):411-9. doi: 10.1002/pca.1066. [PMID: 18446766]
  • Anshu Rathi, Arvind Kumar Srivastava, Annie Shirwaikar, Ajay Kumar Singh Rawat, Shanta Mehrotra. Hepatoprotective potential of Fumaria indica Pugsley whole plant extracts, fractions and an isolated alkaloid protopine. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2008 Jun; 15(6-7):470-7. doi: 10.1016/j.phymed.2007.11.010. [PMID: 18164606]
  • Katherine G Zulak, Aalim M Weljie, Hans J Vogel, Peter J Facchini. Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures. BMC plant biology. 2008 Jan; 8(?):5. doi: 10.1186/1471-2229-8-5. [PMID: 18211706]
  • Sonja Sturm, Christoph Seger, Markus Godejohann, Manfred Spraul, Hermann Stuppner. Conventional sample enrichment strategies combined with high-performance liquid chromatography-solid phase extraction-nuclear magnetic resonance analysis allows analyte identification from a single minuscule Corydalis solida plant tuber. Journal of chromatography. A. 2007 Sep; 1163(1-2):138-44. doi: 10.1016/j.chroma.2007.06.029. [PMID: 17628575]
  • Xianghua Xiao, Juntian Liu, Jingwen Hu, Tianxia Li, Yuanhui Zhang. Protective effect of protopine on the focal cerebral ischaemic injury in rats. Basic & clinical pharmacology & toxicology. 2007 Aug; 101(2):85-9. doi: 10.1111/j.1742-7843.2007.00075.x. [PMID: 17651307]
  • David K Liscombe, Peter J Facchini. Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy. The Journal of biological chemistry. 2007 May; 282(20):14741-51. doi: 10.1074/jbc.m611908200. [PMID: 17389594]
  • Katherine G Zulak, Anthony Cornish, Timothy E Daskalchuk, Michael K Deyholos, Dayan B Goodenowe, Paul M K Gordon, Darren Klassen, Lawrence E Pelcher, Christoph W Sensen, Peter J Facchini. Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism. Planta. 2007 Apr; 225(5):1085-106. doi: 10.1007/s00425-006-0419-5. [PMID: 17077972]
  • Jürgen Schmidt, Chotima Boettcher, Christine Kuhnt, Toni M Kutchan, Meinhart H Zenk. Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding. Phytochemistry. 2007 Jan; 68(2):189-202. doi: 10.1016/j.phytochem.2006.10.003. [PMID: 17113612]
  • Ilkay Orhana, Berrin Ozçelik, Taner Karaoğlu, Bilge Sener. Antiviral and antimicrobial profiles of selected isoquinoline alkaloids from Fumaria and Corydalis species. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2007 Jan; 62(1-2):19-26. doi: 10.1515/znc-2007-1-204. [PMID: 17425100]
  • Yi-Chen Chia, Fang-Rong Chang, Chin-Chung Wu, Che-Ming Teng, Keh-Shaw Chen, Yang-Chang Wu. Effect of isoquinoline alkaloids of different structural types on antiplatelet aggregation in vitro. Planta medica. 2006 Oct; 72(13):1238-41. doi: 10.1055/s-2006-947196. [PMID: 16981134]
  • Lin-Feng Xu, Wen-Jing Chu, Xiao-Yun Qing, Sheng Li, Xue-Song Wang, Guo-Wei Qing, Jian Fei, Li-He Guo. Protopine inhibits serotonin transporter and noradrenaline transporter and has the antidepressant-like effect in mice models. Neuropharmacology. 2006 Jun; 50(8):934-40. doi: 10.1016/j.neuropharm.2006.01.003. [PMID: 16530230]
  • H Heinle, D Hagelauer, U Pascht, O Kelber, D Weiser. Intestinal spasmolytic effects of STW 5 (Iberogast) and its components. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2006; 13 Suppl 5(?):75-9. doi: 10.1016/j.phymed.2006.03.013. [PMID: 16709451]
  • Kwan Ho Lee, Jae-Wan Huh, Myung-Min Choi, Seung Yong Yoon, Seung-Ju Yang, Hea Nam Hong, Sung-Woo Cho. Regulation of glutamate level in rat brain through activation of glutamate dehydrogenase by Corydalis ternata. Experimental & molecular medicine. 2005 Aug; 37(4):371-7. doi: 10.1038/emm.2005.47. [PMID: 16155414]
  • Priyamvada Singh, Vinay K Singh, Dinesh K Singh. Effect of binary combination of some plant-derived molluscicides with MGK-264 or piperonyl butoxide on the reproduction of the snail Lymnaea acuminata. Pest management science. 2005 Feb; 61(2):204-8. doi: 10.1002/ps.936. [PMID: 15619718]
  • Bo Jiang, Kun Cao, Rui Wang. Inhibitory effect of protopine on K(ATP) channel subunits expressed in HEK-293 cells. European journal of pharmacology. 2004 Dec; 506(2):93-100. doi: 10.1016/j.ejphar.2004.11.004. [PMID: 15588728]
  • Paul M Wynne, John H Vine, R Gary Amiet. Protopine alkaloids in horse urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Nov; 811(1):85-91. doi: 10.1016/j.jchromb.2004.03.077. [PMID: 15458726]
  • Dae Keun Kim, Ki Taek Lee, Nam-In Baek, Sung-Hoon Kim, Hee Wook Park, Jong Pil Lim, Tae Yong Shin, Dong Ok Eom, Jae Heon Yang, Jae Soon Eun. Acetylcholinesterase inhibitors from the aerial parts of Corydalis speciosa. Archives of pharmacal research. 2004 Nov; 27(11):1127-31. doi: 10.1007/bf02975117. [PMID: 15595415]
  • Tian-qing Yan, Yan-fang Yang, Tie-min Ai. [Determination of protopine and isocorydine in root of Dactylicapnos scandens by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2004 Oct; 29(10):961-3. doi: . [PMID: 15631083]
  • K Morteza-Semnani, Gh Amin, M R Shidfar, H Hadizadeh, A Shafiee. Antifungal activity of the methanolic extract and alkaloids of Glaucium oxylobum. Fitoterapia. 2003 Jul; 74(5):493-6. doi: 10.1016/s0367-326x(03)00113-8. [PMID: 12837370]
  • Liane D Paul, Hans H Maurer. Studies on the metabolism and toxicological detection of the Eschscholtzia californica alkaloids californine and protopine in urine using gas chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Jun; 789(1):43-57. doi: 10.1016/s1570-0232(03)00124-7. [PMID: 12726842]
  • Gail B Mahady, Susan L Pendland, Adenia Stoia, Lucas R Chadwick. In vitro susceptibility of Helicobacter pylori to isoquinoline alkaloids from Sanguinaria canadensis and Hydrastis canadensis. Phytotherapy research : PTR. 2003 Mar; 17(3):217-21. doi: 10.1002/ptr.1108. [PMID: 12672149]
  • Yuh-Chwen Chang, Pei-Wen Hsieh, Fang-Rong Chang, Ru-Rong Wu, Chih-Chuang Liaw, Kuo-Hsiung Lee, Yang-Chang Wu. Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from formosan Argemone mexicana. Planta medica. 2003 Feb; 69(2):148-52. doi: 10.1055/s-2003-37710. [PMID: 12624820]
  • Julia Serkedjieva, Maria Velcheva. In vitro anti-influenza virus activity of isoquinoline alkaloids from thalictrum species. Planta medica. 2003 Feb; 69(2):153-4. doi: 10.1055/s-2003-37720. [PMID: 12624821]
  • H Saglam, G Arar. Cytotoxic activity and quality control determinations on Chelidonium majus. Fitoterapia. 2003 Feb; 74(1-2):127-9. doi: 10.1016/s0367-326x(02)00312-x. [PMID: 12628406]
  • R Suau, B Cabezudo, R Rico, F Nájera, J M López-Romero. Direct determination of alkaloid contents in Fumaria species by GC-MS. Phytochemical analysis : PCA. 2002 Nov; 13(6):363-7. doi: 10.1002/pca.669. [PMID: 12494757]
  • D L Yang, X N Huang, A S Sun, B Huang, L Ye, J S Shi. [RP-HPLC method for determination of protopine in plasma and pharmacokinetics in rats]. Yao xue xue bao = Acta pharmaceutica Sinica. 2001 Oct; 36(10):790-2. doi: NULL. [PMID: 12579983]
  • A K Salmore, M D Hunter. Elevational trends in defense chemistry, vegetation, and reproduction in Sanguinaria canadensis. Journal of chemical ecology. 2001 Sep; 27(9):1713-27. doi: 10.1023/a:1010411122739. [PMID: 11545366]
  • J J Chen, Y L Chang, C M Teng, W Y Lin, Y C Chen, I S Chen. A new tetrahydroprotoberberine N-oxide alkaloid and anti-platelet aggregation constituents of Corydalis tashiroi. Planta medica. 2001 Jul; 67(5):423-7. doi: 10.1055/s-2001-15820. [PMID: 11488455]
  • J Dostál, Z Zák, M Necas, J Slavík, M Potácek. Protopine hydrochloride. Acta crystallographica. Section C, Crystal structure communications. 2001 May; 57(Pt 5):651-2. doi: 10.1107/s0108270101003249. [PMID: 11353282]
  • F Du, S Wang, Z Xie. [Concentration of four alkaloids in the aerial parts of Eomecon chionantha from different mounth in year]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2000 Apr; 23(4):189-90. doi: ". [PMID: 12575122]
  • S Singh, D K Singh. Effect of molluscicidal components of Abrus precatorius, Argemone mexicana and Nerium indicum on certain biochemical parameters of Lymnaea acuminata. Phytotherapy research : PTR. 1999 May; 13(3):210-3. doi: 10.1002/(sici)1099-1573(199905)13:3<210::aid-ptr421>3.0.co;2-f. [PMID: 10353159]
  • K O Hiller, M Ghorbani, H Schilcher. Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pig ileum. Planta medica. 1998 Dec; 64(8):758-60. doi: 10.1055/s-2006-957576. [PMID: 9933996]
  • K H Janbaz, S A Saeed, A H Gilani. An assessment of the potential of protopine to inhibit microsomal drug metabolising enzymes and prevent chemical-induced hepatotoxicity in rodents. Pharmacological research. 1998 Sep; 38(3):215-9. doi: 10.1006/phrs.1998.0353. [PMID: 9782072]
  • L Rastrelli, A Capasso, C Pizza, N De Tommasi, L Sorrentino. New protopine and benzyltetrahydroprotoberberine alkaloids from Aristolochia constricta and their activity on isolated guinea-pig ileum. Journal of natural products. 1997 Nov; 60(11):1065-9. doi: 10.1021/np960710b. [PMID: 9392875]
  • H L Wei, G T Liu. [Protective action of corynoline, acetylcorynoline and protopine against experimental liver injury in mice]. Yao xue xue bao = Acta pharmaceutica Sinica. 1997 May; 32(5):331-6. doi: . [PMID: 11498866]
  • F N Ko, T S Wu, S T Lu, Y C Wu, T F Huang, C M Teng. Antiplatelet effects of protopine isolated from Corydalis tubers. Thrombosis research. 1989 Oct; 56(2):289-98. doi: 10.1016/0049-3848(89)90170-9. [PMID: 2559491]
  • D Y Wang. [Effects of alkaloids of Corydalis decumbens on cerebral and peripheral circulation in the dog]. Zhong xi yi jie he za zhi = Chinese journal of modern developments in traditional medicine. 1986 Aug; 6(8):477-9, 454. doi: ". [PMID: 2947718]
  • L Y He, Y B Zhang. [TLC separation and densitometric determination of six isoquinoline alkaloids in Corydalis bungeana]. Yao xue xue bao = Acta pharmaceutica Sinica. 1985 May; 20(5):377-82. doi: ". [PMID: 4083024]